7. I remember the kilbourn days as lots of "fat and ugly" jokes

and not so much substance. The show got tons better with Stewart.

In fact Liz Winstead, the creator of The Daily Show did:

The show was much less politically focused than it later became under Jon Stewart, having what Stephen Colbert described as a local news feel and involving more character-driven humor as opposed to news-driven humor. Winstead recalls that when the show was first launched there was constant debate regarding what the show's focus should be. While she wanted a more news-driven focus, the network was concerned that this would not appeal to viewers and pushed for "a little more of a hybrid of entertainment and politics". The show was slammed by some reviewers as being too mean-spirited, particularly towards the interview subjects of field pieces; a criticism acknowledged by some of the show's cast. Describing his time as a correspondent under Kilborn, Colbert says, "You wanted to take your soul off, put it on a wire hanger, and leave it in the closet before you got on the plane to do one of these pieces." One reviewer from The New York Times criticized the show for being too cruel and for lacking a central editorial vision or ideology, describing it as "bereft of an ideological or artistic center... precocious but empty."

There were reports of backstage friction between Kilborn and some of the female staff, particularly the show's co-creator Lizz Winstead. Winstead had not been involved in the hiring of Kilborn, and disagreed with him over what direction the show should take. "I spent eight months developing and staffing a show and seeking a tone with producers and writers. Somebody else put him in place. There were bound to be problems. I viewed the show as content-driven; he viewed it as host-driven," she said. In a 1997 Esquire magazine interview, Kilborn made a sexually explicit joke about Winstead. Comedy Central responded by suspending Kilborn without pay for one week, and Winstead quit soon after.
In 1998, Kilborn left The Daily Show in order to replace Tom Snyder on CBS's The Late Late Show. He claimed the "Five Questions" interview segment as intellectual property, disallowing any future Daily Show hosts from using it in their interviews. Correspondents Brian Unger and A. Whitney Brown left the show shortly before him, but the majority of the show's crew and writing staff stayed on. Kilborn's last show as host aired on December 17, 1998. Reruns were shown until Jon Stewart's debut four weeks later.